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| 19/08/2019 | 16:00 | FK Novo Crnilishte | - | FK Bregalnica Štip | 0:22 | |
| 20/08/2019 | 16:00 | FK Ljuboten | - | GFK Tikvesh | 1:5 | |
| 16:00 | FK Kit-Go Pehčevo | - | FK Pelister | 4:5 pso | ||
| 21/08/2019 | 16:00 | FK Fortuna | - | Sileks Kratovo | 0:4 | |
| 16:00 | FK Ohrid | - | FK Belasica | 5:4 pso | ||
| 16:00 | FK Kravari | - | FK Labuništa | 1:4 | ||
| 16:00 | KF Gostivari | - | KF Shkëndija 79 | 1:4 | ||
| 16:00 | FK Osogovo | - | FK Pobeda Junior | 1:0 | ||
| 16:00 | FK Vlazrimi 77 | - | FK Rabotnički | 0:4 | ||
| 16:00 | Prevalec | - | FK Borec | 0:4 | ||
| 16:00 | Lokomotiva Skopje | - | FC Struga | 1:5 | ||
| 16:00 | FK Kožuf | - | FK Renova | 5:6 pso | ||
| 16:00 | FK Teteks | - | KF Shkupi | 1:5 | ||
| 28/08/2019 | 16:00 | Kamenica Sasa | - | Vardar Skopje | 0:5 |
